


An Angel in the Middle

by HornedQueenOfHell



Category: Supernatural
Genre: AU, Castiel panics, Failed one night stand, I used the AU last names, M/M, Mistaken Identity, Only Wincest if you want, Other, Polyamory, Wincestiel - Freeform, night club
Language: English
Status: Completed
Published: 2016-06-13
Updated: 2016-06-13
Packaged: 2018-07-14 18:21:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,315
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7185011
Author URL: https://archiveofourown.org/users/HornedQueenOfHell/pseuds/HornedQueenOfHell
Summary: <blockquote class="userstuff">
              <p>“I have a surprise for you.”<br/>“What is it?” Dean asked rubbing his thumb over the side of Sam’s hand.<br/>“Pick someone, anyone. Doesn’t matter what gender, and if it’s alright, we’ll take them home with us.”</p>
            </blockquote>





	An Angel in the Middle

**Author's Note:**

> I am not a fan of incest hence the Smith and Wesson names but feel free to consider it wincest if you want.

Dean really hadn’t wanted to be here, really hadn’t. He only came because Sam wanted to spoil him and Dean could never say no to his lover. They sat in the classy nightclub sipping drinks, Dean tucked underneath Sam’s arm as they casually pointed out people and made up insane backstories for them trying to get the other to blow their drink out their nose.  


“Oh that one over there with the blonde hair. She’s a demon who sold her soul years ago, her name is Meg and she wants to rule the world with her demon army. But get this they all ride unicorns.” Dean snorted, laughing uproariously because he was more than a little drunk, “Wait why, why did she sell her soul?”  


“To have a hot pizzaman/babysitter roleplay with an angel.” Sam whispered causing Dean to go red. He thought Sam had been asleep when he watched that.  


“How did you know about that?!”  


“You aren’t exactly quiet Dee, and you had the volume cranked up.” Dean crossed his arms and grumbled under his breath until Sam placated him with small kisses along his face and neck. Dean ran his his fingers along the cufflinks he’d given the taller man for his birthday. ‘SW’ Sam Wesson, and ironically Dean’s last name was Smith.

They were CEO’s of one of the largest steel manufacturers this side of the Atlantic. Unfortunately the Smith and Wesson gun company did not find the similar name amusing and threatened to sue them if they gave their company the same name. Winchester rifles was their first client and the company was named after them in honor of it. As the company grew Sam and Dean became known as the Winchesters and they ran with it. Those who didn’t know the men were together thought them to be brothers.

Sam flipped his hand over and threaded his fingers with Dean’s, pulling the older man from his thoughts.  


“I have a surprise for you.”  


“What is it?” Dean asked rubbing his thumb over the side of Sam’s hand.  


“Pick someone, anyone. Doesn’t matter what gender, and if it’s alright, we’ll take them home with us.”  


“You’re serious, Sammy you don’t have to do that. You know I’m happy with you right.”  


“‘Course I do Dee, and this is something I want to do with you too. Having someone with us, pending on they type of person they are the possibilities are endless.” Dean smiled and squeezed Sam’s knee under the table, they had spoken about it a few times, things like this, but Sam had never liked the idea as much as Dean. He wasn’t sure what had changed Sam’s mind but once the taller man did it was after a lot of careful thoughts and contemplation. 

Dean scanned the room, narrowing down the few men and women he found attractive enough for a night with, he was pushing his attention in the direction of a pretty blonde with a great rack when a flash of blue on the dance floor pulled his eyes in another direction. Thick, black, sex hair framed the widest blue eyes he’d ever seen but that wasn’t what caught his attention, those hips did though. Dean smiled when he saw the tie matching his eyes, hanging backwards none the less. Clearly dressed for business but he was having a good time and mother of god he was a delicious looking man.  


“Blue tie, next to the candy addict.” Dean indicated with his chin, Sam scanned the floor taking note of the short man who had been the recipient of one of Dean’s greatest backstories; and then he finally found the man Dean was looking at and he sucked his breath, yeah he was beautiful.  


“I call first dibs on that hair.” Dean panted next to him.  


“I’m leaning toward that mouth myself, he has nice lips. Lets see if he’s interested.” Sam stood from his seat and held a hand out for Dean who gladly pulled himself into Sam’s body. They moved out to the dance floor and kept an eye on their target. After a few minutes they caught him dancing alone and with a glance at each other Dean and Sam knew it was time. They were standing next to the man now so Dean leaned over and tapped his elbow, his breath caught when the full force of those baby blues were turned his way but he took a moment to compose himself then held a hand out in invitation. Laser focus and a slight frowny face of confusion raked over them both zeroing in on their clasped hands and Sam’s open smile. 

After a few moments hesitation his strong, calloused fingers slid into Dean’s hand. Dean’s grin turned positively evil as he yanked the man between them their arms caging him in as the next song started playing.  


“Hello angel.” Dean chuckled, the deep smell of the man’s cologne was intoxicating and Dean found himself leaning closer to breathe it in his fingers on Sam’s hip tightening.  


“Hello.” Both men shuddered, they had not expected a voice like that.  


“Care to dance with us?” Sam asked letting his fingers skim over the strangers sides.  


“I fear that statement is a bit redundant as we are already dancing.”  


“The fuck? Are you from a Shakespeare novel?”  


“No?” The guy seemed confused now.  


“Ignore him, anything older than the 1970’s gives him a headache, he can’t understand class.”  


“Hey I like James Bond.” Dean pouted. By now they had all figured out how to move together and they could feel their chosen beginning to loosen up between them.  


“I don’t understand that reference and Shakespeare wrote plays not novels.” Sam laughed in the man’s ear and it caused a small shiver to roll down his spine, good at least he seemed interested. The way he pushed back against Sam was another good indicator. Dean’s thumb had found it’s way under the guys dress shirt and was outlining the edge of his hip, he must have found a sensitive spot because the guy threw his head back and practically melted into Sam. Taking advantage of his position Dean let his fingers curl into his hair and keep his head back to get at that pale neck. Soon the man was panting softly between them, small whimpers escaping his lips as his hips shifted softly against Dean’s leg. Sam was rubbing teasing lines by the crease of his leg, also ‘accidentally’ brushing against Dean to make him let out a few whimpers as well.  


“May I kiss you?” Sam asked, the guy nodded and so Sam claimed his lips softly. Dean groaned and got even harder pushing his hands under Sam’s belt. When they broke apart Dean decided it was time to move this party.  


“Come home with us.” He demanded rolling his hips into the shorter man’s. He had one arm wound around Sam’s neck and felt pretty impressive against Dean’s thigh.  


“I-I don’t even know your names.” He gasped trying to catch his breath, yeah Sam had that effect on you. Dean and Sam glanced at each other, hesitating on which name before answering.  


“Sam Wesson, that’s Dean Smith. You?” The man took a moment to answer,  


“James or Jim Milton.”  


“Well James, would you like to come home with us?” James nodded his head looking at the both of them.  


“Very much.” Both men smiled in relief and Jimmy gave them a small smile back. He couldn’t believe his luck, two gorgeous men who wanted him, this was unbelievable.  


“You drive here?” Sam asked, he seemed to be the most practical of them, Jimmy nodded,  


“I can follow you.” Dean clapped him on the shoulder before grabbing Sam and tugging him along,  


“Then let’s get this show on the road!” Jimmy gave a small smile before following them out. When he finally got to his car he took a deep breath, now that he was out of the club he could think. Gabriel had forced him out tonight to celebrate the fact that he’d gotten an interview with his dream company. The fact that it was tomorrow was irrelevant to him. Jimmy rested his head on his hands and waited to see Sam and Dean again, if those were their real names. They were beautiful men and again the black haired man found himself wondering what they wanted with him, they were clearly together and he hardly wanted to be used between them. Milton’s cheeks flamed when he realized his wording. Before he could back out and run home with his tail between his legs, a large black car with two happily waving seducers pointed him to the exit they were taking. Biting his lip he shifted his car into gear and followed them.  


Dean clapped a hand on Sam’s leg as they pulled into their place, they were both pretty glad James hadn’t chickened out and couldn’t wait to get him inside. They parked the Impala, and went to go meet Jimmy in the driveway.  


“You still good?” Sam asked hand ghosting over their partner's elbow, thumb rubbing soft circles over his trench coat.  


“I am, but are you both sure about this?” He murmured. Dean glanced over at Sam before dipping down to kiss the shorter man on the lips. Jimmy gasped which Dean took advantage of before yanking the dark haired man into their garage.  


“We are, we want you.” Once the garage was closed and they were in the house Sam helped Dean crush James between them and ravish him. He was panting and writhing between them when they finally broke apart yanking James upstairs and trading sweet kisses as they stripped off their clothes. Both men pushed James to the bed as Dean stripped Sam of the last items of his clothes, James was watching with rapt attention as Sam trailed his fingers down Dean’s back, scratching at his skin just enough to make him shudder. Sam winked at Jimmy over Dean’s shoulder and the dark haired man swallowed audibly, this might actually kill him. Soon Dean joined James on the bed, easily pinning him down while Sam traced Dean’s spine with his tongue now. Sam’s fingers trace up James’ legs and started tracing his nails left to right, just barely teasing the inside of his thighs. 

Dean slid out from between them to grab supplies while Sam wrapped Jimmy’s legs around his waist and ground his hips hard into the man. James growled and flipped them, rotating his hips over Sam’s and smirking when he gets the tall man to throw his head back and grip the sheets tightly.  


“My turn.” He nipped Sam’s ear, sucking on his neck. He decided he wanted his hands elsewhere and pulled on those long, thick locks which made Sam whimper. Dean came back while he was occupied and palmed his ass before trailing kisses across his lower back. He worked his way up over each knob of Jimmy’s spine, whispering sweet nothings. James collapsed, writhing on Sam’s broad chest when Dean found the sensitive spot on the back of his neck and abused it. Sam hooked his ankle behind Dean’s calf pulling him closer, Dean smiled and twined their fingers together which Jimmy watched curiously. He might have been between them but he was hardly in the middle of them, he wished he could find a love like that someday. Sam noticed his gaze and turned his head to kiss Jimmy’s wrist drawing the shorter man’s attention.  


“Are you a top or bottom?” Sam murmured against his skin, working his way up his arm with slow, wet kisses.  


“Both, I am not picky. Right now though I’m feeling very bottom if that’s alright with you.”  


“Sure, that’s fine. Would you like Dean to fuck you first, or me?” Jimmy glanced down at Sam and whimpered,  


“Dean, please.” Sam chuckled and ran his fingers through Jimmy’s hair which the man leaned into.  


“Can’t say I blame you just figured I’d give you the option.” The dark haired man responded by kissing him breathless, Jimmy could feel Sam smile into the kiss and responded with his own. Dean had worked his way back down to Jimmy’s ass and uncapped the lube.  


“Ready angel?” He asked and Jimmy nodded moving his hands from Sam’s hair to the bedsheets. Dean was very slow and careful prepping him, only moving when he knew James was ready as Sam helped distract him from the discomfort of the stretch with small kisses and nips until he was giving small whimpers and cries into Sam’s neck. Dean got a condom on and moved around to the open side of the bed and kneeled on the comforter reaching to roll Jimmy over and claim his swollen lips before pulling the smaller man into his lap. He pushed in slowly keeping one hand splayed over Jimmy’s stomach and abdomen, feeling it quiver as his head lolled back onto Dean’s shoulder. He sucked in a breath and shuddered when he felt Dean slide home entirely. 

To Jimmy’s surprise Dean reached out and gripped his hand bringing his inner wrist up so Dean could kiss over the same spot Sam did. Good god that is hot, he couldn’t help but think, unknown to him the others were thinking the exact same thing.  


“I’m okay, you can move.” He panted, clenching his muscles slightly and enjoying the way it caused Dean to scratch his nails lightly across James’ skin. Sam stroked himself slowly watching the two of them together, he almost wanted a photo they were so beautiful. When Dean started to pull out Sam slipped forward placing his legs on either side of Dean’s caging them all together. He rubbed a thumb across one of James’ nipples loving the small shudder that rolled down his spine and Dean pushed back in. They couple worked in tandem picking up speed and pressure until Cas was dribbling pre-come steadily and biting his lip to hold back the small mewls of pleasure that came at a near constant rate.  


“Dean, I’m going to come. Dean please.” He begged, Sam wrapped a few long fingers around the base of Jimmy’s cock helping him stave off his orgasm as Dean pulled out carefully. Sam gave Jimmy a few minutes to cool down as he pulled the condom off and sucked Dean down. Dean came swearing and clutching onto Sam’s back, the younger pulled off and turned James to face him and pulled his lips open to share the salty kiss between them.  


“Fuck, fuck, fuck.” Dean repeated gripping his oversensitive cock tightly, watching the two of them together was enough to make anyone get it up again quick. Sam paused to grab a condom and roll it on, he would’ve loved to have the shorter man bare but they had no idea if he was clean or if he’d lie about it if asked. 

Last thing he needed was something like genital herpes. 

Jimmy groaned and slithered closer to Sam rubbing their penis’ together and panting for more. Sam gripped Jimmy’s arms and pinned him down, settling between the dark haired man’s legs. He pushed three fingers, with a little more lube, into the man’s entrance and made sure he was still okay with this.  


“Yes, please. Please fuck me Sam.” With a quick kiss to his cheek Sam complied. Jimmy was not a screamer but even he could not deny that Sam was big, he reached farther than Dean had and the head of Sam’s dick pressed right over his prostate.  


“Fuck!”The smaller man cried wriggling as he adjusted to the new size, Dean openly admired Jimmy’s wantonness between them. There were not enough hours in the day to detail how much and how many ways he would love to share James Milton between himself and Sam.  


“Jesus James.” Sam hissed, Jimmy was just smirking so Dean decided to join the game again and leave a beautiful hickey on the man's collar bone. Sam fucked James a lot harder and faster than Dean had, but he was a natural top. James’ stunning blue eyes flashed in Dean’s direction and one of his recently freed hands trailed down to the top of Dean’s ass, he glanced up questioningly at the dirty blonde only sliding down when Dean nodded enthusiastically. The tip of one slim finger trailed over his hole before sliding lower to fondle his balls for a bit, eventually the finger came back though and just barely pressed in causing Dean to whine. After a few moments the tip of that finger was keeping pace with the pace Sam was pounding into Jimmy. Dean swore and rocked his hips with the finger wanting just a little bit more.  


“Touch yourself?” Jimmy asked. Dean nodded and wrapped his fingers around himself almost completely hard again. Sam swore and snapped his hips harder causing Jimmy to throw his head back and cry out, he was clearly on the verge of coming and Sam too by the looks of it. Jimmy began to rock his hips up to meet Sam’s thrusts as the tall man gripped Jimmy’s erection and began stroking him quickly. Jimmy came quickly body almost convulsing from the force of his orgasm. Dean orgasmed after that even though he did not come, no clean up meant no complaints. Sam finished after a few more thrusts as James mewled through his own aftershocks. 

Sam pulled out gently kissing along Jimmy’s cheekbone as he did, he snorted as Dean and Jimmy curled up together in the center of the bed. Smacking Dean’s ass as he passed he went to get a cloth to clean them up, when he came back Jimmy had drifted off and Dean was petting his hair. Carefully they washed him off, before cleaning each other off. Sam pushed Dean back into the middle watching the blond carefully settle an arm across their companions side, sliding in behind his lover Sam placed a soft kiss on Dean’s ear.  


“What are you thinking?” He whispered,  


“I want to keep him. Is that wrong?” Dean asked his eyes flitting over James’ beautiful features.  


“Only if you were the only one thinking it.” Dean tilts his head back,  


“So you like him too.” Sam smiles and nods,  


“Maybe, we’ll discuss it with him in the morning, see how he feels.” Dean bumps his forehead against Sam’s affectionately,  


“I love you Sammy, thank you for everything, for being with me.”  


“I love you too Dean, never forget that.” Kissing Dean softly Sam skims his nose across Dean’s jaw before kissing the back of his neck and settling there. The couple soon joins their companion in sleep.

Jimmy stirs just before dawn and startles when he realizes he is not in an empty bed, he places his hands over his mouth when he remember exactly what he did last night. Slinking out of the bed he scrambles for his clothes praying he doesn’t wake them. As he buttons his shirt back up he looks at the two of them entwined together. 

Figures, best sex of his life and they’re both taken, by each other. Still though they had made room for him and god the sex was incredible, he considered pausing to kiss them goodbye but he didn’t want to wake them and he refused to leave a note. They were so beautiful, he knew walking out their door was going to be hard, but he had an interview to get ready for. 

He fled their house and made it back to his double time. Gabriel was snoring on his couch when he let himself in, the dark haired man let out a sigh of relief and went to change into running clothes. He was thinking he’d take it a little easier today though, he was pretty sore. He hopped in the shower when he was finished and managed to get one cup of coffee in his system before Gabriel woke up.  


“Hey, where’d you go last night? The blond grumbled, rubbing his eyes and holding his head, a cup of coffee appeared on the coffee table and Gabriel curled around it purring like a cat.  


“You wouldn’t believe me if I told you.” The man smirked causing Gabriel to scowl.  


“I remember you dancing with a couple of guys, you go home with one of them?” Smirking of the rim of his coffee he couldn’t help but reply,  


“No, both of them.” Gabriel paused for a moment then began laughing,  


“Bullshit, no way did you- vanilla sex extraordinaire- manage to bang two guys at the same time. That was good, I needed that.” Gabriel said still giggling every now and again. Shrugging the dark haired man placed his coffee cup in the sink and stretched.  


“I’m going to get a little work done before my interview, don’t puke on my couch.”  


“Whatever.” Gabriel grunted curling back up to sleep off his hangover.

“Okay boys this is your last one of the morning.” Said a chipper, sarcastic laden voice.  


“Thanks Meg, send ‘em up.”Sam replied, he was far more tolerant of the sass filled vixen than Dean. After a few moments the intercom came on again.  


“Lord that boy is sex on a stick, that voice, those eyes. Oh Clarence you can be my unicorn any day.” That got a snort out of Dean who pressed the button to respond,  


“Let’s see if we even to keep this one before I have to draw up the sexual harassment papers.” Meg responded by blowing him a raspberry. Rolling his eyes Dean turned back to the resume in front of him,  


“I hope this guy is halfway competent, his file is impressive. He’d be a good fit for us.”  


“We can only hope.” Sam commented from where he was perched on the edge of the desk reading over Dean’s shoulder. At the top of the page was printed ‘Castiel Novak’, the door opened shortly after and Dean and Sam’s jaws dropped.  


“Jimmy?!”  


Castiel’s head snapped up at the familiar voices and he blanched.  


“Sam? Dean? What are you doing here?” Everyone blinked at each other a few times.  


“We own the company, what are you doing here?”  


“I’m here for the interview.” Dean looked from the paper, up to the man, then back down and up. Sam recovered first.  


“Why did you run off this morning, we thought we had done something wrong or hurt you.” Cas’ eyes widened.  


“No, no not at all. I just had to check on my brother and I run in the mornings so I’m always up early.”  


“Well Shit Ji-Castiel, we were going to at least cook you breakfast.” Now Cas was the one taken aback,  


“Oh um thank you that was kind of you to think that. I’m sorry for leaving but you both are together and I thought, well that if you’re together why did you even want me in the first place.” Cas was starting to panic now.  


“Dean has very open views on sex, ones I share. I was more reluctant about this than him, but I was curious and wanted to at least try and you were perfect. We wanted to ask if you’d like to keep doing this.”  


“This being secret casual sex?”  


“A polyamorous relationship, with all three of us.”  


“But-but why? You are the CEO’s of a massive corporation and you already have each other what the hell do want with someone like me?”  


“Someone like you?” Dean asked, he picked up Castiel’s resume and flipped through it, “You are dedicated, intelligent, fine as hell and our top candidate for this position. Your references are commendable and your track record is spotless; we want to give you a job and if you are willing a place in our bed and our lives.” Castiel swallowed and forced himself from wringing his tie in nervousness.  


“Perhaps, we could get through the interview first and then maybe have dinner tonight to talk about this.”  


“That is satisfactory.” Sam said settling on the edge of the desk closest to Castiel now. Dean smiled and asked the first question, half an hour later they knew they were going to hire Castiel Novak. After a round of handshakes and a quick kiss on the cheek from the pair Cas left the building and went back to his home. Gabriel was in the shower so Cas began to clean and find small tasks to do to keep his mind off what was going to happen tonight.  


“Hey bro how’d the interview go?” Gabriel asked emerging from his room in fresh clothes.  


“I’m confident.” he replied.  


“Get any calls from your two sexy lovers from last night?” Cas snickered,  


“Not exactly, see they own the company I interviewed for today and even asked me to dinner tonight in hopes of continuing our relationship together.” Gabe scoffed and heading onto the kitchen to make lunch.  


“You’re a weird one Cassie.” Eventually time rolled around though, Dean and Sam has his number from his resume and texted him a time and a place. Dressed as best he could without feeling like he was overdoing it he headed out. Sam and Dean were out front waiting for him, holding hands. Cas swallowed nervously and approached them, they smiled brightly and waved glad he showed up. They did want things to work between them.  


“Glad you could make it Cas.” Dean sneaked a hand onto his ass as they headed into the restaurant. They found a table and got settled as waters arrived for them.  


“So I have to ask, who is Jimmy Milton?” Dean asked taking a sip of his drink.  


“Oh, he’s my identical twin.” Dean about blew his water out of his nose at that.  


“Twins?!” Oh yes, they were so keeping him.

**Author's Note:**

> You can find me around, come say hi!
> 
> DA: http://civil-war-casualty.deviantart.com/  
> Tumblr: http://hornedqueenofhell.tumblr.com/


End file.
